Sodium borohydride → HCID 22181282, compound

Participants

Reaction Steps

2-(4-ethoxybenzoyl)-N,N-diethyl-1-(3-methylbutyl)-1H-benzimidazole-5-carboxamide (110 mg, 0.252 mmol) was dissolved in 3 mL of EtOH. NaBH4 (12 mg, 1.2 eq) was added and the solution stirred at rt for 1 h. The solvent was concentrated and the residue dissolved in EtOAc. The organic phase was washed with saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was directly purified by reversed-phase chromatography (C-18 column) using a gradient of 10–65% CH3CN/H2O and then lyophilized affording the title compound. The product was isolated as the corresponding TFA salt. Yield: 102 mg (73%); 1H NMR (400 MHz, CD3OD) δ 7.85 (br s, 2H), 7.62 (br s, 1H), 7.40 (br s, 2H), 7.01 (br s, 2H), 6.33 (br s, 1H), 4.29 (br s, 2H), 4.06 (br s, 2H), 3.62 (br s, 2H), 3.32 (br s, 2H), 1.55 (br, 2H), 1.38 (br s, 3H), 1.30 (br s, 3H), 1.17 (br s, 2H), 0.90 (s, 3H), 0.83 (s, 3H); MS (ESI) (M+H)+=438.30; Anal. Calcd for C26H35N3O3+1.2 TFA: C, 59.38; H, 6.35; N, 7.32. Found: C, 59.36; H, 5.97; N, 7.37.

Provenance & Evidence